(1S,5R)-1-(tert-Butyl-dimethyl-silanyloxy)-6-(toluene-4-sulfonyl)-6-aza-bicyclo[3.2.1]oct-2-ene

Base Information

Chemical Name:(1S,5R)-1-(tert-Butyl-dimethyl-silanyloxy)-6-(toluene-4-sulfonyl)-6-aza-bicyclo[3.2.1]oct-2-ene
CAS No.:289710-27-6
Molecular Formula:C₂₀H₃₁NO₃SSi
Molecular Weight:393.623
Hs Code.:

Synonyms:(1S,5R)-1-(tert-Butyl-dimethyl-silanyloxy)-6-(toluene-4-sulfonyl)-6-aza-bicyclo[3.2.1]oct-2-ene

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Chemical Property of (1S,5R)-1-(tert-Butyl-dimethyl-silanyloxy)-6-(toluene-4-sulfonyl)-6-aza-bicyclo[3.2.1]oct-2-ene

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Technology Process of (1S,5R)-1-(tert-Butyl-dimethyl-silanyloxy)-6-(toluene-4-sulfonyl)-6-aza-bicyclo[3.2.1]oct-2-ene

There total 8 articles about (1S,5R)-1-(tert-Butyl-dimethyl-silanyloxy)-6-(toluene-4-sulfonyl)-6-aza-bicyclo[3.2.1]oct-2-ene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 261156-79-0
(E)-3-[(2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-acrylonitrile

: 289710-27-6
(1S,5R)-1-(tert-Butyl-dimethyl-silanyloxy)-6-(toluene-4-sulfonyl)-6-aza-bicyclo[3.2.1]oct-2-ene

Guidance literature:: Multi-step reaction with 7 steps

1: 98 percent / H₂ / Pd/C / ethyl acetate / 12 h / 760.05 Torr

2: 100 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C

3: 84 percent / Jones reagent / acetone / 0.5 h / 20 °C

4: 78 percent / SmI₂; MeOH / tetrahydrofuran / -78 - 20 °C

5: 91 percent / DIPEA / CH₂Cl₂ / 17 h / 0 - 20 °C

6: methanol / 20 h / 0 - 20 °C

7: 1.3 g / NaH / toluene / 3 h / Heating

With methanol; jones reagent; samarium diiodide; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; acetone; toluene; 1: Catalytic hydrogenation / 2: desilylation / 3: Oxidation / 4: Cyclization / 5: Condensation / 6: Condensation / 7: Reduction;
DOI:10.1021/jo000260z

Reference yield:

: C₁₄H₁₇NO₃SSiC₆H₁₄N₂HSO₂C₇H₇

: 289710-27-6
(1S,5R)-1-(tert-Butyl-dimethyl-silanyloxy)-6-(toluene-4-sulfonyl)-6-aza-bicyclo[3.2.1]oct-2-ene

Guidance literature:: With sodium hydride; In toluene; for 3h; Heating;
DOI:10.1021/jo000260z

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 289710-27-6
(1S,5R)-1-(tert-Butyl-dimethyl-silanyloxy)-6-(toluene-4-sulfonyl)-6-aza-bicyclo[3.2.1]oct-2-ene

Guidance literature:: Multi-step reaction with 3 steps

1: 91 percent / DIPEA / CH₂Cl₂ / 17 h / 0 - 20 °C

2: methanol / 20 h / 0 - 20 °C

3: 1.3 g / NaH / toluene / 3 h / Heating

With sodium hydride; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; toluene; 1: Condensation / 2: Condensation / 3: Reduction;
DOI:10.1021/jo000260z